반응 #309762

반응 방정식

sodium carbonate

hydrogen fluoride

polyethylene

1-oxa-spiro[2.4]heptane-2-carbonitrile

→

desired compound

수율 58.1%

(1-Fluoro-cyclopentyl)-hydroxy-acetonitrile

수율 58.1%

용매

pyridine

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도The mixture is cooled at 0° C.
2. 2
   추출The aqueous layer is extracted with diethyl ether
3. 3
   세척washed with water and brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   기타the solvent is removed
7. 7
   기타The residue is purified by chromatography in a 20 g silica gel cartridge
8. 8
   세척eluting with hexane:diethyl ether (100:0 to 80:20)

실험 절차

Anhydrous dichloromethane (3 mL) and a 70% w/w solution of hydrogen fluoride (2.68 mL, 20.44 mmol) in pyridine are mixed in a polyethylene bottle at 0° C. under a nitrogen atmosphere. A solution of 1-oxa-spiro[2.4]heptane-2-carbonitrile (3.30 g, 26.76 mmol) in anhydrous dichloromethane (3.2 mL) is added slowly. The reaction is stirred at 0° C. for 1 h and at room temperature for 1 h. The mixture is cooled at 0° C. and a saturated solution of sodium carbonate is added carefully. The aqueous layer is extracted with diethyl ether. The organic layers are combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the solvent is removed. The residue is purified by chromatography in a 20 g silica gel cartridge eluting with hexane:diethyl ether (100:0 to 80:20) to obtain 1.7 g of desired compound as a colourless oil. 1H NMR (CDCl3) δ (ppm): 4.47 (d, 1H), 3.50 (bs, 1H), 2.12-1.67 (m, 8H).

출처